Do not like to suffer from heat in Italy...?

Good to know. We have gone in March, but were wondering about January sometime.

We will soon be on our way and sooooooo looking forward to being their in winter!! Five nights in Florence w/o heat and intense crowds . . . yes please :) :)

I generally travel in last spring/early summer or fall (may to early June or October). I’ve thought about winter but am unsure about comfort walking/eating outside. Can you comfortably wander streets and drink wine on the square in winter? Or is most of your time inside sights (also valuable!)?

We live in Minnesota.
Our family went to Athens, Greece over New Year's.
Our sons wore shorts and got many stares from the heavily clad locals.

In Florence, on average, you'll have highs of 50 and lows about 35.
Sun / Rain / Wind / .... you have to pack for more of a range of weather.

We were in Spain two years ago, in April, and it was colder than I wanted :-(
One of our AirBnb places didn't have heat. The owner had ONE portable heater that tripped the circuit breaker. He brought a second one but it barely dented the problem. COLD.

There were already a lot of people that already travel to Italy in January February or March

Of my 5 visits to Italy, 3 of them (all 3+ weeks) have been in February and have been wonderful, in spite of the occasional rain and chill - from the north (Venice) to the south (Amalfi Coast). Gelato tastes just as good in winter and Italian hot chocolate is divine.